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[ CAS No. 66947-92-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 66947-92-0
Chemical Structure| 66947-92-0
Chemical Structure| 66947-92-0
Structure of 66947-92-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 66947-92-0 ]

CAS No. :66947-92-0 MDL No. :MFCD00468672
Formula : C9H8N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :DNGZINUIRBDWED-UHFFFAOYSA-N
M.W : 208.24 Pubchem ID :829035
Synonyms :

Calculated chemistry of [ 66947-92-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.3
TPSA : 93.45 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 1.88
Log Po/w (WLOGP) : 1.67
Log Po/w (MLOGP) : 1.17
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 1.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.456 mg/ml ; 0.00219 mol/l
Class : Soluble
Log S (Ali) : -3.46
Solubility : 0.0715 mg/ml ; 0.000343 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.69
Solubility : 0.421 mg/ml ; 0.00202 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 66947-92-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 66947-92-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 66947-92-0 ]
  • Downstream synthetic route of [ 66947-92-0 ]

[ 66947-92-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 66947-92-0 ]
  • [ 73931-63-2 ]
Reference: [1] Synthetic Communications, 1980, vol. 10, # 3, p. 167 - 174
  • 2
  • [ 66947-92-0 ]
  • [ 93-85-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 17, p. 4982 - 4986
  • 3
  • [ 66947-92-0 ]
  • [ 22514-58-5 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With lithium hydroxide; water In tetrahydrofuran at 0 - 20℃;
Stage #2: With hydrogenchloride; water In tetrahydrofuran
2-Bromo-benzothiazole-6-carboxylic acid; [00105] To a solution of 2-bromo-benzothiazole-6-carboxylic acid methyl ester (1.256 g, 4.39 mmol) in THF (60 mL) and H2O (20 mL) is added lithium hydroxide monohydrate (920 mg, 21.9 mmol) at 0 0C. The mixture is stirred at rt overnight. The mixture is treated with IN HCl solution to adjust pH to 2 and extracted with ethyl acetate. The organic phase is washed with brine. The solvent is removed in vacuo and the crude product is used for next step without further purification. MS(ESI) m/z: 257.9 (M+l) +.
Reference: [1] Patent: WO2008/124393, 2008, A1, . Location in patent: Page/Page column 33-34
  • 4
  • [ 66947-92-0 ]
  • [ 1024583-33-2 ]
YieldReaction ConditionsOperation in experiment
88% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; 2-Bromo-benzothiazole-6-carboxylic acid methyl ester; <n="35"/>[00104] To a solution of 2-amino-benzothiazole-6-carboxylic acid methyl ester (1.11 g, 5 mmol) and CuBr2 (2.23 g, 10 mmol) in CH3CN (50 mL) is added tert-butyl nitrite (1.32 mL, 90percent, 10 mmol) at 0 0C. The mixture is stirred at rt overnight. The mixture is extracted with ethyl acetate. The organic phase is washed with saturated NaHCO3 solution and brine. The solvent is removed in vacuo and the crude product is purified using flash chromatography (hexane: ethyl acetate/10: 1) to give 2-bromo-benzothiazole-6-carboxylic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 8.53 (d, IH), 8.15 (dd, IH), 8.01 (d, IH), 4.42 (q, 2H), 1.42 (t, 3H). MS(ESI) m/z: 271.9 (M+l) +.
27% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 30℃; Inert atmosphere To a 250 rnL rmmd-hottom flask, purged and maintained under
18% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 20℃; To a stirred mixture of VIII-2 (600 mg, 2.28 mmol) and CuBr2 (775 mg, 3.46 mmol) in MeCN (9 mL) was added tert-butyl nitrite (445 mg, 4.32 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with EtOAc (40 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column (PE:EA=5:1) to give VIII-3 (140 mg, yield: 18percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2324 - 2328
[2] Patent: WO2008/124393, 2008, A1, . Location in patent: Page/Page column 33-34
[3] Patent: WO2018/39386, 2018, A1, . Location in patent: Page/Page column 138; 139
[4] Patent: US2014/200215, 2014, A1, . Location in patent: Paragraph 0984; 0986
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